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Maui: 8-Day Itinerary

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Hawaii has always been on our bucket list but we always thought it was just a dream. The dream started to look more achievable after an unfortunate cancellation of an Alaskan Cruise we were supposed to go on it August of 2020. We were stuck with a pretty large airfare credit and it needed to be used. Luck would have it that Alaska Air also flies to Hawaii. Our 10 year anniversary is this year so we thought it was the perfect time to cross off Hawaii from our bucket list. My husband and I, along with another couple, decided Maui as our destination and we had the trip of a lifetime! Here is what we did!

Day 1:

We ended up flying from Detroit to Seattle and then Seattle to Maui. It was 10 hours of flights and pretty exhausting. I was able to pack everything into my under seat “personal item” and a carryon. I was super impressed with myself.

Jumpsuit (similar)t // Under seat Bag // Carryon

The only was this was even possible was because of these amazing compression packing cubes!

Packing Cubes

Since it is a 6 hour time change we actually arrived a 2pm their time! We grabbed our rental car from the lot (we used TURO on this trip and HIGHLY recommend) and headed to Costco to stock up on some essentials. We arrived at our rental and got settled in. We found our 2 bedroom condo right on the beach on VRBO. We had amazing views from our balcony and SOOO MANY sea turtles!

Day 2:

Day two we had to be up BRIGHT AND EARLY, I’m talking 4AM to get to a sport’s fishing charter we had booked. I was in charge of booking and selected Finest Kind Sportfishing out of Lahaina. We choose the 6 hour charter and a shared boat meaning two other people could go with us that we didn’t know (it was a cheaper option). Luck would have it that it just ended up being the 4 of us. We left before sunrise.

Watching the sun rise over Maui

4 hours in and we hadn’t caught anything. I definitely was getting a little anxious since I was the one that booked this and knew all eyes were on me. But just like all fishing sometimes the reward is worth the wait. We ended up getting not one but TWO striped Marlin’s. It was a successful day!

Two Striped Marlin
Super awkward and gross to hold like this

After fishing it was lunch time and we were STARVING! We headed across the street to what I will consider one of the BEST meals on Maui on I had!

Paia Fish Market – Front St

Paia Fish Market was so good!! I had the best Mahi Mahi I have ever had! Highly recommend!! Later that day we headed back out for dinner and drinks. Our first stop was Monkey Pod. We went there because we had heard they had the BEST Mai Tai on the island, which they did. There cocktails were all very impressive.

Mai Tai at Monkey Pod

Fair warning, Monkey Pod’s is NOT on the beach and we decided we would really like a view with dinner so after our drink we left and headed to the Marriott in Wailea. The property itself is breathtaking.

Marriott in Wailea

We did find it was a little pricier than we wanted for dinner so we just had another cocktail and enjoyed the beautiful sunset.

The Marriott at Wailea // Top // Skirt

We headed back to the condo and enjoyed the restaurant there which serves AMAZING Indian Cuisine.

Day 3:

The men decided to golf this day so I planned a hiking trip for my girlfriend and I. Let me preface this by saying we are NOT experienced hikers but wanted to get out and really see Maui. I googled some destinations and came across one I thought would be amazing. It was the Waihee Ridge Trail, and it was amazing, but HARD. My girlfriend and I both workout almost daily and this was challenging but also so rewarding. I mean check out these views!!

Wahiee Ridge Trail

The guys were still not done golfing when we finished so we talked with some locals and headed to a cool spot that suggested. Iao Valley which turned out to be exactly where a fresh stream that we had seen on our last hike was located.

Iao Valley State Park

After that we picked up the guys from golfing and planned our next adventure! We had an “itch” after that to do more hiking even though we were EXHAUSTED. We talked our husbands into heading out to the Lava Fields and doing a quick trail there to see the sunset. It’s the Hoapili Trail to Hanamanioa Point Lighthouse hike but unfortunately we got there too late to do the whole thing but it was still awesome to see the Lava Fields.

Molokini from the Lava Fields
There was a small cave under there.

Day 4:

Up bright and early on day 4 to go Sailing and Snorkeling in the Molokini Crater! We booked this excursion through Sail Trilogy. They have lots of different options but we choose the Discover Molokini. They fed us amazing cinnamon rolls for breakfast on our way to the crater. There we snorkeled and saw amazing sea life!

We then got back on the boat and headed to Turtle Town! We were able to see two sea turtles!

On the way back they opened up the sails and it was so pretty!!

The men went golfing again when we got back and we headed up to the countryside of Kula. The elevation was crazy and it was pretty scary navigating the switchbacks especially because there were no guard rails. We made it up to Maui Wine and each had a tasting. They specialize in pineapple wine.

View at Maui Wine

We stopped at road side stands on the way back and grabbed their famous banana bread and fresh strawberries!

Day 5:

We went all the up the Haleakalā National Park. Our husbands joined us. It was a lot like the drive the day before to the countryside with LOTS of switchbacks all the way up to the summit. Since the summit is at 10,000 ft elevation one thing to remember (which we did not) is that it is MUCH COLDER at the top of the summit than it is beach side. We went earlier in the day and I was in a tank and shorts and when we stepped out of the car it was 38 degrees and SUPER windy! It warmed up as we went but it was COLD. Thank goodness I’m from Michigan and could tough it out! This hike is easy to start. It’s all down hill into the crater but remember, what you do down, you must come up!

Haleakalā National Park

Day 6

Road to Hana! This was a must for me. So many people tried to talk us out of it but I really wanted to do it. It is a WHOLE DAY trip. We move quick and could have made it in 10 hours but there was a fire on the way back that shut down the only way out. I will say we got lucky. If we has decided to do this trip on our own we would not have seen what we were hoping to. The day before I had decided to download the Shaka Guide app for Maui. I purchased the “Classic Road to Hana” and have never made a better decision. There is NO service on the road to Hana so if we didn’t have this app (which works by tracking your GPS location) we would have had no idea where to stop or turn off or find the small hole in the hill that’s actually an entrance to a Lava Tube. 100% recommend the app.

Sea Turtles and Surfing at Ho’okipa Beach Park
Beautiful views the whole way
Small walk through Ko’olau Forest Reserve
Lava Tube
So many waterfalls // Tank // Shorts

At the end of the road to Hana is the other side of the Haleakalā National Park. There is Pipiwai Trail which is about a 4 mile out and back trail through an amazing bamboo forest that ends at Waimoku Falls. This was the HIGHLIGHT of the Road to Hana and can not be missed!!

Bamboo Forest
Waimoku Falls

We really thought nothing could top it but our guide said he had something special left that not a lot of people knew about and that we’d pass it on the way back. When I tell you the directions were “Park after the bridge, hop over the guard rail, go through a cow gate, walk a small path through a pasture and turn right when you find the old grill.” I am not lying. BUT we followed directions and ended at Venus Pools. It wasn’t very crowded, maybe 20 people and a lot of them locals. They were all rock jumping and of course we had to follow suit.

Cliff jumping at Venus Pools

After cliff jumping we decided to head back to our condo. It was a long day but we are happy we did it.

Day 7:

Last full day! The guys really wanted to golf Kapalua and being a golfer myself I REALLY wanted to see the course, so we went with them. The golf course charged a small fee for us to ride in the carts with our husbands.

17th hole of The Bay

I even got to take a couple swings.

This was the only day it rained for us, but we powered through!

Zella Jacket // Dress

Day 8:

Day 8 we flew back home. The airport was extremely busy when we went and the TSA line was well over an hour so back sure to plan ahead!

Recap:

I went into this vacation ready to lay on the beach or by the pool reading my books while our husbands golfed. Maybe do a little shopping. I can tell you I only put my swimsuit on twice. Once we got there I just had a sudden urge that I wanted to go and explore. I can go to the beach and pool at home but I really wanted to experience Maui and I can say that I did!

Let me know if you have any questions!

~Julie // Sisters that Shop